EP2648808B1 - Compositions comprenant des composés d'ammonium quaternaire - Google Patents

Compositions comprenant des composés d'ammonium quaternaire Download PDF

Info

Publication number
EP2648808B1
EP2648808B1 EP11807639.7A EP11807639A EP2648808B1 EP 2648808 B1 EP2648808 B1 EP 2648808B1 EP 11807639 A EP11807639 A EP 11807639A EP 2648808 B1 EP2648808 B1 EP 2648808B1
Authority
EP
European Patent Office
Prior art keywords
weight
composition
group
compositions
carbon atoms
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
EP11807639.7A
Other languages
German (de)
English (en)
Other versions
EP2648808A2 (fr
Inventor
Marc Arderiu Girame
Noemi Casafont Moncunill
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Thor Especialidades SA
Original Assignee
Thor Especialidades SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Thor Especialidades SA filed Critical Thor Especialidades SA
Priority to EP11807639.7A priority Critical patent/EP2648808B1/fr
Publication of EP2648808A2 publication Critical patent/EP2648808A2/fr
Application granted granted Critical
Publication of EP2648808B1 publication Critical patent/EP2648808B1/fr
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0241—Containing particulates characterized by their shape and/or structure
    • A61K8/0254—Platelets; Flakes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair

Definitions

  • the invention relates to the fields of chemistry and personal care products and provides additives which are useful and convenient for formulating shampoos, conditioners.
  • Fatty quaternary ammonium compositions are useful additives to hair care products such as shampoos, conditioners.
  • quats are useful additives to hair care products such as shampoos, conditioners.
  • U.S. Patent No. 4,891,214 issuing to Stevens et al. on January 2nd, 1999 provides an informative background into quats and their uses.
  • the above mentioned requirements can be achieved by adding short-chain alcohols, in particular isopropanol or ethanol, in amounts of from 15 to 20% by weight.
  • the short-chain alcohols are volatile organic solvents which raise significant environmental and safety concerns, not only for the manufacturer but also both for the consumer and for the company formulating the personal care products. Therefore, it is desirable to find other, non-volatile solvent/formulation systems.
  • compositions containing quats and fatty alcohols do not share the same problem with volatility and can be flakeable.
  • fatty alcohols such as cetearyl alcohol have been used as quat solvents.
  • these compositions have a quat content of less than 35%.
  • Attempts to increase the cationic activity, namely the amount of quat used, up to 35% leads to products with melting points typically over 100°C and in order to effectively handle and, ultimately, flake the material, it must often be heated to a point near, or above this temperature, in which the quat can begin to degrade.
  • this relatively high content of fatty alcohol tends to dramatically increase the viscosity of the finished product.
  • the short-chain alcohols can be replaced by linear fatty alcohols, e. g. cetyl alcohol, lauryl alcohol, behenyl alcohol, or stearyl alcohol and alkyl glycols, such as for example, propylene glycol or 1,3-butandiol, which are additionally added in order to lower the setting point or melting point of the mixtures to temperatures below 100 °C.
  • linear fatty alcohols e. g. cetyl alcohol, lauryl alcohol, behenyl alcohol, or stearyl alcohol and alkyl glycols, such as for example, propylene glycol or 1,3-butandiol, which are additionally added in order to lower the setting point or melting point of the mixtures to temperatures below 100 °C.
  • alkyl glycols mentioned in WO 00/28950 A1 could be also used alone as solvent systems for quats. However, they have a number of drawbacks. First, quats containing glycols as a solvent generally result in formulations which are not flakable. Instead, they form a so what viscous, waxy "gummy" solid. While this material may have a lower overall melting point than the fatty alcohol based solvent quats, the overall handling problems involved from this material are significantly greater.
  • glycols are typically coming from synthetic sources.
  • Today's personal care market is challenged to find innovative, natural alternatives to synthetic and petroleum-based chemicals that have similar or better performance.
  • EP 1 269 992 B1 discloses compositions comprising quaternary ammonium compounds and at least one polyhydric alcohol having 5 to 12 carbon atoms. According to the teaching of this document, these compositions shall have low setting and melting points, good dispersability in aqueous media and have a low flashpoint. According to a preferred embodiment these compositions are free from fatty alcohols and linear or branched monoalcohols having 8 to 36 carbon atoms.
  • the compositions disclosed in EP 1 269 992 B1 shall have low setting points and being nevertheless sufficiently hard and brittle at room temperature to allow pelleting or flaking, what solves the first drawback of the use of glycols as a sole solvent system. However, these polyhydric alcohols are also typically coming from synthetic sources.
  • each attempt to increase the quat content in the compositions while obtaining the desirable commercial handling properties of quats falls short in one aspect or another.
  • Use of water as a solvent generally results in compositions with a comparatively low quat-content.
  • Use of short-alkyl alcohols as a solvent is problematical due to their high organic volatility.
  • Glycols, whether used alone or in combination with fatty alcohols, are generally petrochemical derivatives and unpopular in personal care applications.
  • the use of solvent systems comprising long chain alkyl fatty alcohols what leads to products with better environmental profile, results in low cationic activity of the quats and requires heating the resulting product to a point in which the quats begin to degrade.
  • compositions comprising quaternary ammonium compounds, at least one glycerol monoester of a C 12-24 fatty acid and fatty alcohols generally result in formulations which have low setting and melting points, good dispersability in aqueous media by maintaining the cationic activity of the quat, wherein the amount of the quat in the composition is particularly preferably higher than 40% and more preferably at least 50% by weight.
  • the concentrated compositions of the present invention can be free from short chain alcohols, in particular isopropanol and glycols such as for example propylene glycol or 1,3-butandiol.
  • the novel compositions are thus formulated with only solvents based from renewable resources, achieve a high active matter of about 50% by weight and are thus highly suitable for formulating quaternary ammonium compounds for personal care applications.
  • compositions comprising, based on the finished composition,
  • the relative portions of a) to b) to c) depends somewhat on the quat used and the glycerol monoester and fatty alcohol mixture used.
  • the fluidity of the composition of the invention is important from a manufacturing standpoint because without the proper final commercial handling properties, it will be extremely difficult to produce a commercially feasible product. During manufacture, the product has to be stirred, heated, cooled as needed and often transferred in a fluid state to a flaking or a pastillation line. All of this needs to be achieved at commercially viable temperatures, temperatures which will not degrade the quat.
  • the proportion of quaternary ammonium compounds (a) based on the finished composition is 40 to 60 % per weight, particularly preferably 45 to 55 % by weight, especially preferably 50 % by weight. Surprisingly it has been found, that the compositions can advantageously have high portions by weight of quaternary ammonium compounds (a) coupled with simultaneously low melting and setting points.
  • Quaternary ammonium compounds a) are preferably (C 12 -C 36 )-, preferably (C 14 -C 24 )-, practically preferably (C 16 -C 24 )-alkyltrimethylamonium compounds. Particular preference is given to alkyltrimethylammonium compounds in which the alkyl radical is a behenyl, erucyl, cetyl or stearyl radical.
  • the anion X- in Formula (1) maybe any desired charge-balancing anion; according to the invention, the anion is an anion selected from the group consisting of chloride, iodide, bromide, methosulfate, hydrogensulfate, lactate, citrate, carbonate and bicarbonate or a mixture thereof.
  • a very particularly suitable quaternary ammonium compound a) is behenyltrimethylammonium chloride.
  • the proportion of glycerol monoesters or the proportion of the glycerol monoester b) is, based on the finished compositions, 15 to 25 % by weight, particularly preferably 17 to 23 % by weight, especially preferably 20% by weight.
  • Glycerol monoesters selected from the group consisting of glycerol monoester of one or more C 12-24 fatty acid(s), b), are to be understood as meaning fatty acid monoesters with glycerol, wherein the fatty acid is a saturated or unsaturated fatty acid.
  • the fatty acid is selected from the group consisting of lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, myristoleic acid, palmitoleic acid, sapienic acid, oleic acid and arichidonic acid.
  • glycerol monoesters can include glycerol monostearate, glycerol monopalmitate, glycerol arachidate, glycerol oleate, glycerol laurate and mixtures thereof.
  • the glycerol monoester, constituent b) of the composition of the invention is selected from the group consisting of glycerol monostearate and/or glycerol monopalmitate.
  • constituent b) is glycerol monostearate wherein the fatty acid is a mixture 50:50 % by weight of palmitic acid and stearic acid.
  • the proportion of fatty alcohols having 10 to 20 carbon atoms, constituent c) of the composition of the invention is, based on the finished compositions, 25 to 35 % by weight, particularly preferably 27 to 33 % by weight, especially preferably 30 % by weight.
  • Constituent c) is characterized in that it comprises:
  • constituent (ca) to constituent (cb) from 1,0 to 1,5, preferably from 1,0 to 1,2, leads to compositions with low setting and melting points, which are fluid enough to be manufactured feasible and flakeable.
  • fatty alcohols having 10 to 20 carbon atoms, c) are mixtures selected of a the group consisting of capric alcohol (1-decanol), lauryl alcohol (1-dodecanol), myristyl alcohol (1-tetradecanol), cetyl alcohol (1-hexadecanol), stearyl alcohol (1-octadecanol), oleyl alcohol (cis-9-Octadecen-1-ol) and arachidyl alcohol (1-eicosanol).
  • the fatty alcohols, compounds (c) are selected from the group consisting of 1-dodecanol, 1-tetradecanol, 1-hexadecanol and 1-octadecanol.
  • the composition consists of 50% by weight of behenyltrimethylammonium chloride, 20% by weight of glyceryl monostearate, 4,5% by weight of 1-hexadecanol, 10,5% by weight of 1-octadecanol, 10,5% by weight of 1-dodecanol, and 4,5% by weight of 1-tetradecanol.
  • compositions of the invention preferably have setting points below 100 °C, very particularly preferably below 95 °C.
  • compositions according to the invention may for example be in a form selected from the group consisting of pellets, flakes, extrudates, pastes, compacts, emulsions, dispersions, and mixtures thereof. According to a preferred embodiment the compositions are in the form of pellets or flakes. Flakes or pellets are desired in the commercial industry because they are easily handled and incorporated into desired products.
  • compositions are free-flowing liquids over their setting points, making them easy to manufacture and easy to transfer and pump through transfer lines to flaking or pastillation equipment when it is chilled below its melting point and either broken into easy to handle flakes or dispensed into pellets/pastilles and cooled.
  • the claimed compositions generally require the setting point to be below 100°C in order to facilitate the transfer to the flaking lines while maintaining the integrity of the quats in the composition. More preferably the setting point of the compositions is below 95 °C. Whether a formulation is flakable is measured by pouring a relatively thin film of the heated composition onto a metal sheet and allowing it to cool. The cooled film is then "crumbled” or “scraped” into small flakes by any type of mechanical process.
  • a successful composition must possess two properties. First, the composition must possess the property of being easily poured onto the sheet plus forming a thin film. Second, once the composition is allowed to cool, it must brake into flakes after crumbling or scrapping. These flakes are consequently easily stored and re-melted as necessary.
  • Pastillation is a process in which small amounts of the desired formulation are dispensed into pastilles/pellets. These pastilles are then allowed to cool, forming a product which is in solid form but easy returned to liquid state. Whether a formulation is escapable of pastillation is measurable by distributing small amounts of the heated formulation into pastilles. These pastilles are then allowed to cool. The pastilles must be easily melted without tremendous amounts of heat, preferably below the boiling point of water.
  • compositions of the present invention are generally suitable for the preparation of products / compositions comprising quaternary ammonium compounds.
  • compositions are particularly suitable for the preparation of cosmetics, dermatological and pharmaceutical products.
  • the invention accordingly also provides for the use of the compositions according to the invention for the preparation of products, preferably cosmetics, dermatological and pharmaceutical compositions in particular hair treatment compositions, comprising quaternary ammonium compounds.
  • Examples of preferred products are shampoos, rinse-off hair conditioners, cream rinsers, clear rinsers, hair cures, hair colorants and hair tints, permanent waiving compositions, hair gels, hair conditioners in aerosol, spray and fluid form, two-in-one shower preparations, cream shower preparations, skin care compositions, day creams, night creams, care creams, nutrient creams, body lotions and ointments.
  • the cosmetic, dermatological and pharmaceutical products or compositions comprise the compositions according to the invention, based on the finished product preferably in amounts of from 0.1 to 15% by weight, particularly preferably 1 to 10% by weigh.
  • the cosmetic, dermatological and pharmaceutical products can comprise as further auxiliaries and additives, all customary surfactants, oily substances, emulsifiers and co-emulsifiers, cationic polymers, film formers, super fatting agents, moisture donating agents, stabilizers, biogenic active ingredients, preservatives, pearlizing agents, dyes and fragrances, solvents, glycerol, hydrotrophic agents, opacifiers, thickeners, dispersions, protein derivatives, such as gelatines, collagen hydrolysates, natural and synthetic-based polypeptides, egg yolk, lecithin, lanolin and lanolin derivatives, silicones, deodorizing agents, substances with a keratolytic and keratoplastic action, enzymes, carrier substances, and antioxidants, UV-Light protection filters, pigments and metal oxides and antimicrobially effective agents.
  • all customary surfactants such as gelatines, collagen hydrolysates, natural and synthetic-based polypeptides, egg yolk, lecithin
  • a composition of 50% by weight of behenyltrimethylammonium chloride is prepared in a known manner by alkylation of a tertiary amine with methyl chloride in the presence of the following solvent types and ratios: Glyceryl stearate: 20% by weight C 18 alcohol: 10,5% by weight C 16 alcohol: 4,5% by weight C 14 alcohol: 4,5% by weight C 12 alcohol: 10,5% by weight
  • Phase Component Percentage (%wt) A Demineralized water Qsp 100% Tetrasodium EDTA 0.05 Citric acid 0.05 B Hydroxyethylcellulose (HEC) 0.75 Glycerin 2 C Steareth-21 1 Quat Qsp 0.5% active matter D Cetyl alcohol 2.5 F Preservative (Microcare ® IT, Thor) 0.075 Fragrance 0.5 Total 100%
  • Example 1 The product composition of the Example 1 gives similar results when comparing both wet combing and formula viscosity than a standard Behentrimonium chloride with Isopropanol.
  • Example Active* (%) Glyceryl Stearate C 18 alcohol [% by wt] C 16 alcohol [% by wt] C 14 alcohol [% by wt] C 12 alcohol [% by wt] Comments 2 50 50 0 0 0 0 NPF 3 50 0 35 15 0 0 NPF 4 50 0 0 0 15 35 v: 5570 cp 5 50 0 21 9 6 14 NPF 6 50 20 21 9 0 0 NPF 7 50 20 0 0 9 21 v: 8320 cp 8 50 30 7 3 3 7 NPF 9 34 0 33 33 0 0 v: 17580 * Active: Behentrimonium chloride [% by weight] NPF: not production feasible (setting points higher than 100°C) v: Viscosity of the final formula (20°C after 1 week, RvM4V10 1')

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (8)

  1. Composition comprenant, sur la base de la composition finie,
    a) de 40 à 60% en poids d'au moins un composé quaternaire selon la formule (1)
    Figure imgb0004
     dans laquelle R1 est un groupement alkyle ou alcényle non ramifié ou ramifié ayant de 12 à 36 atomes de carbone, un groupement R5CONH(CH2)n- ou un groupement R5COO(CH2)n-, où R5 est un groupement alkyle ou alcényle ayant de 12 à 36 atomes de carbone et n est un nombre allant de 1 à 8, et
    R2, R3 et R4 sont indépendamment les uns des autres, peuvent être identiques et sont un groupement -CH3, CH3CH2-, CH3CH2CH2-, CH3CH2CH2CH2-, -CH2CH2OH ou -CH2CH(OH)CH2OH, et X- est un anion choisi dans le groupe constitué par le chlorure, l'iodure, le bromure, le méthosulfate, l'hydrogénosulfate, le lactate, le citrate, le carbonate et le bicarbonate, ou des mélanges de ceux-ci, et
    b) de 15 à 25% en poids d'au moins un monoester de glycérol choisi dans le groupe constitué par un monoester de glycérol d'un acide gras en C12-24, et
    c) de 25 à 35% en poids d'un mélange d'alcools gras ayant de 10 à 20 atomes de carbone,
    caractérisé en ce que ledit mélange d'alcools gras comprend :
    (ca) au moins un alcool gras ayant de 10 à 14 atomes de carbone, et
    (cb) au moins un alcool gras ayant de 16 à 20 atomes de carbone,
    où le rapport pondéral de (ca) à (cb) va de 1,0 à 1,5.
  2. Composition selon la revendication 1, dans laquelle les composés d'ammonium quaternaire, les composés a), sont des composés de (C12-C36)-, préférablement de (C14-C24)-, particulièrement préférablement de (C16-C24)-alkyltriméthylammonium.
  3. Composition selon la revendication 1 ou 2, dans laquelle le composé d'ammonium quaternaire, le composé a), est le chlorure de béhényltriméthylammonium.
  4. Composition selon les revendications 1 à 3, dans laquelle le au moins un monoester de glycérol, le composé b), est le monostéarate de glycérol.
  5. Composition selon les revendications 1 à 4, dans laquelle les alcools gras, les composés c), sont choisis dans le groupe constitué par le 1-dodécanol, le 1-tétradécanol, le 1-hexadécanol et le 1-octadécanol.
  6. Composition selon les revendications 1 à 5, dans laquelle la composition est constituée de 50% en poids de chlorure de béhényltriméthylammonium, 20% en poids de monostéarate de glycérol, 4,5% en poids de 1-hexadécanol, 10,5% en poids de 1-octadécanol, 10,5% en poids de 1-dodécanol, et 4,5% en poids de 1-tétradécanol.
  7. Composition selon les revendications 1 à 6, qui se trouve sous la forme de pastilles ou de paillettes.
  8. Composition selon les revendications 1 à 7, ayant un poids de solidification inférieur à 95°C.
EP11807639.7A 2010-12-10 2011-12-08 Compositions comprenant des composés d'ammonium quaternaire Active EP2648808B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP11807639.7A EP2648808B1 (fr) 2010-12-10 2011-12-08 Compositions comprenant des composés d'ammonium quaternaire

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP10015509 2010-12-10
EP11807639.7A EP2648808B1 (fr) 2010-12-10 2011-12-08 Compositions comprenant des composés d'ammonium quaternaire
PCT/EP2011/006186 WO2012076177A2 (fr) 2010-12-10 2011-12-08 Compositions comprenant des composés d'ammonium quaternaire

Publications (2)

Publication Number Publication Date
EP2648808A2 EP2648808A2 (fr) 2013-10-16
EP2648808B1 true EP2648808B1 (fr) 2015-03-18

Family

ID=45470503

Family Applications (1)

Application Number Title Priority Date Filing Date
EP11807639.7A Active EP2648808B1 (fr) 2010-12-10 2011-12-08 Compositions comprenant des composés d'ammonium quaternaire

Country Status (4)

Country Link
US (1) US20130251655A1 (fr)
EP (1) EP2648808B1 (fr)
ES (1) ES2538651T3 (fr)
WO (1) WO2012076177A2 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102012223197A1 (de) 2012-12-14 2014-06-18 Henkel Ag & Co. Kgaa Wasserfreie Zusammensetzungen gegen Körpergeruch
SG11202013227UA (en) * 2018-07-12 2021-01-28 Stepan Co Esterquat compositions

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3689478T2 (de) * 1986-10-23 1994-07-21 Witco Corp Teilchenförmiges emulgierbares haarkonditioniermittel.
US4886660A (en) * 1987-06-11 1989-12-12 Colgate-Palmolive Company Shine hair conditioner
DE3837860A1 (de) * 1988-11-08 1990-05-10 Wella Ag Lagerstabiles haarkonditionierungsmittel mit perlglanz
US5989533A (en) * 1997-07-21 1999-11-23 Revlon Consumer Products Corporation Hair conditioning compositions containing alpha or beta hydroxy acid esters
WO2000028950A1 (fr) * 1998-11-12 2000-05-25 Croda, Inc. Compositions d'ammonium quaternaire gras
DE10009996B4 (de) * 2000-03-02 2005-10-13 Cognis Ip Management Gmbh Feststoffgranulate mit monodisperser Korngrößenverteilung, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung
DE10126253A1 (de) * 2001-05-29 2002-12-05 Clariant Gmbh Neuartig konfektionierte quaternäre Ammoniumverbindungen
DE10129225A1 (de) * 2001-06-19 2003-01-02 Clariant Gmbh Neuartig konfektionierte quaternäre Ammoniumverbindungen
JP4911877B2 (ja) * 2002-01-09 2012-04-04 クローダ，インコーポレイテッド 第四級化合物の混合物
JP4589050B2 (ja) * 2003-12-22 2010-12-01 日本精化株式会社 ジエステル及び油剤、並びに化粧料及び皮膚外用剤
EP1786521A1 (fr) * 2004-09-09 2007-05-23 Unilever Plc Compositon revitalisante capillaire anhydre

Also Published As

Publication number Publication date
WO2012076177A3 (fr) 2013-12-12
ES2538651T3 (es) 2015-06-23
EP2648808A2 (fr) 2013-10-16
US20130251655A1 (en) 2013-09-26
WO2012076177A2 (fr) 2012-06-14

Similar Documents

Publication Publication Date Title
RU2464012C1 (ru) Композиция для кондиционирования волос
CN1798542B (zh) 含二酯季铵化合物的个人护理产品
US7074395B2 (en) Cosmetic formulations of quaternary ammonium compounds incorporating polyhydric alcohols
BRPI1100869A2 (pt) composições compreendendo compostos de amÈnio quaternário e carbonatos orgánicos
EP1935878B1 (fr) Hydroxyalkylurée pour un effet hydradant amélioré
US6919074B2 (en) Cosmetic formulations of quaternary ammonium compounds free of short-chain alcohols
JP4370078B2 (ja) 新規第四アンモニウム化合物組成物
CN114929182B (zh) 具有含有苯甲酸钠和二醇和/或甘油酯的防腐体系的毛发调理剂组合物
WO2010116941A1 (fr) Produit cosmetique pour les cheveux
EP3532012B1 (fr) Compositions de soins capillaires comprenant des matières qui modifient le sébum
EP2648808B1 (fr) Compositions comprenant des composés d'ammonium quaternaire
JP2004352688A (ja) 防腐剤組成物
WO1998017254A1 (fr) Formulations cosmetiques contenant de la gliadine
CN111372563A (zh) 毛发化妆品
JP3649619B2 (ja) 外用組成物
CN114929183A (zh) 含有二十二烷酰氨基丙基二甲基胺的毛发调理剂组合物
JPH02172908A (ja) エアゾール型毛髪化粧料
JP3649620B2 (ja) 外用組成物
JP2024138105A (ja) 化粧料
JP2022139147A (ja) 固形コンディショナー組成物
JPH0655656B2 (ja) 毛髪化粧料
BRPI0917027B1 (pt) Hair conditioner composition and method of using such composition

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20130618

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

R17D Deferred search report published (corrected)

Effective date: 20131212

RIC1 Information provided on ipc code assigned before grant

Ipc: A61Q 5/12 20060101ALI20140916BHEP

Ipc: A61Q 5/02 20060101AFI20140916BHEP

Ipc: A61K 8/41 20060101ALI20140916BHEP

Ipc: A61K 8/34 20060101ALI20140916BHEP

Ipc: A61K 8/37 20060101ALI20140916BHEP

Ipc: A61K 8/02 20060101ALI20140916BHEP

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

DAX Request for extension of the european patent (deleted)
INTG Intention to grant announced

Effective date: 20141027

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

REG Reference to a national code

Ref country code: CH

Ref legal event code: EP

REG Reference to a national code

Ref country code: IE

Ref legal event code: FG4D

REG Reference to a national code

Ref country code: AT

Ref legal event code: REF

Ref document number: 716155

Country of ref document: AT

Kind code of ref document: T

Effective date: 20150415

REG Reference to a national code

Ref country code: DE

Ref legal event code: R096

Ref document number: 602011014908

Country of ref document: DE

Effective date: 20150507

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2538651

Country of ref document: ES

Kind code of ref document: T3

Effective date: 20150623

REG Reference to a national code

Ref country code: NL

Ref legal event code: VDEP

Effective date: 20150318

REG Reference to a national code

Ref country code: NL

Ref legal event code: VDEP

Effective date: 20150318

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

Ref country code: FI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

Ref country code: HR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

Ref country code: NO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150618

Ref country code: SE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

REG Reference to a national code

Ref country code: AT

Ref legal event code: MK05

Ref document number: 716155

Country of ref document: AT

Kind code of ref document: T

Effective date: 20150318

REG Reference to a national code

Ref country code: LT

Ref legal event code: MG4D

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: RS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

Ref country code: LV

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

Ref country code: GR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150619

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: RO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

Ref country code: EE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

Ref country code: PT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150720

Ref country code: SK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

Ref country code: CZ

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150718

Ref country code: PL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

Ref country code: AT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 5

REG Reference to a national code

Ref country code: DE

Ref legal event code: R097

Ref document number: 602011014908

Country of ref document: DE

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

26N No opposition filed

Effective date: 20151221

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20151231

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MC

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

Ref country code: LU

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151208

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

REG Reference to a national code

Ref country code: IE

Ref legal event code: MM4A

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20151208

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20151231

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20151231

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 6

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BG

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

Ref country code: SM

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

Ref country code: HU

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT; INVALID AB INITIO

Effective date: 20111208

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: CY

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 7

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

Ref country code: TR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: AL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20150318

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20231220

Year of fee payment: 13

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20231220

Year of fee payment: 13

Ref country code: DE

Payment date: 20231214

Year of fee payment: 13

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: ES

Payment date: 20240118

Year of fee payment: 13

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: IT

Payment date: 20231229

Year of fee payment: 13